Methyl formate → HCID 69941877, compound

HRID 1034364Notes

Reaction equation

HRID 1034364 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH:14](OC)=[O:15].[H-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](=[CH:14][OH:15])[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 7865Methyl formateHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 2733232METHYL 2-CHLORO-6-FLUOROPHENYLACETATE

Product 1

HCID 69941877HCID 69941877, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of methyl (2-chloro-6-fluorophenyl)acetate (5.20 g) and methyl formate (31.4 ml) in dry DMF (40 ml) was added dropwise to a stirred suspension of sodium hydride (1.23 g) in dry DMF (40 ml) at a temperature between 0° and 5° C. Vigorous evolution of gas was observed. The reaction mixture was stirred at room temperature for 3.5 hours, then poured into a mixture of ice and aqueous sodium carbonate, and washed with ether. The resulting aqueous mixture was acidified with concentrated hydrochloric acid and extracted with ether. The extracts were washed with water, dried and concentrated to give methyl 2-(2-chloro-6-fluorophenyl)-3-hydroxypropenoate (3.44 g) as a white solid.

Workup

  1. washwashed with ether
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-69e8466f27014edfa2a93735198d1e92
Source dataset
uspto-grants-1994_05
Patent number
US05315025

Reaction notes

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